Originally an intern at The Score, Richards hosted five-minute segments called Cabbie on the Street from 2001 to 2002. After leaving The Score, he joined Sportsnet to produce and host the programs NBAXL and J-Zone, before moving back to The Score in 2005, where he again hosted Cabbie on the Street segments, along with Cabbie Unlimited and Cabbie All Stars. Richards also hosted NBA Court Surfing, before leaving the network again on November 30, 2010. Since 2011, Richards began hosting a weekly segment on TSN's SportsCentre entitled "Cabbie Presents". Richards was a special correspondent on The Marilyn Denis Show on CTV from 2011 to 2012, where he brought a male perspective to conversations about relationships, while also filing reports with Hollywood actors, musicians and everyday Canadians on the street. According to Richards, his particular style of journalism – entertain first, inform second – has allowed him to carve out a unique identity. He often initiates physical contact with the people he interviews, a technique that has gotten mixed reactions from interviewees. His unorthodox and animated style however, has endeared him to many of the A-List athletes he's interviewed. These include stars such as Michael Jordan, Kobe Bryant, Stephen Curry, Aaron Rodgers, Patrick Mahomes, J.J. Watt, Russell Wilson, Alexander Ovechkin, Connor McDavid, Derek Jeter and David Ortiz. Richards' atypical interviews with Kobe Bryant have garnered particular attention. Their frequent collaborations have resulted in the two developing a friendly relationship. Richards' interviews have also spanned into the world of entertainment with celebrities such as Will Smith, Hugh Jackman, Will Ferrell, Kevin Hart, Drake, Wiz Khalifa, A$AP Rocky & Kendrick Lamar.
Cabbie Presents
Richards hosted and produced "Cabbie Presents", a weekly segment which aired Fridays on "Sportscentre" on TSN. "Cabbie Presents" offered a light-hearted slice of life look at professional athletes, with a sketch-based format to the segment. Richards has interviewed LeBron James and Kobe Bryant together, given Aaron Rodgers his own muppet, gifted Patrick Mahomes a yellow one piece suit made iconic by Bruce Lee from the movie Game of Death, had his face covered in vaseline by Mike Tyson at his home and Norman Powell doused him with champagne on the Toronto RaptorsNBA Championship Parade. From 2012 to 2019, Richards also hosted a podcast, "Cabbie Presents: The Podcast", where he interviewed a variety of sports and entertainment stars.
Departure from TSN
Cabbie left TSN on September 6, 2019 to pursue other career aspirations. Thereafter, he began co-hosting a new program on B/R Betting alongside expert Kelly Stewart.
